13116-38-6

Basic information

• Product Name: 9-(3,5-dideoxypentofuranosyl)-9H-purin-6-amine
• CAS NO: 13116-38-6
• Molecular Formula: C₁₀H₁₃N₅O₂
• Molecular Weight: 235.2425
• Mol File: 13116-38-6.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 547°C at 760 mmHg
• Flash Point: 284.6°C
• Density: 1.77g/cm³
• Vapor Pressure: 8.5E-13mmHg at 25°C
• Refractive Index: 1.825
• CAS DataBase Reference: 9-(3,5-dideoxypentofuranosyl)-9H-purin-6-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 9-(3,5-dideoxypentofuranosyl)-9H-purin-6-amine(13116-38-6)
• EPA Substance Registry System: 9-(3,5-dideoxypentofuranosyl)-9H-purin-6-amine(13116-38-6)

Safety Data

• Hazardous Substances Data: 13116-38-6(Hazardous Substances Data)

Upstream product

• 127246-63-3 3',5'-di-O-p-tolylsulphonyladenosine 

Relevant articles and documents

REACTION OF ADENINE NUCLEOSIDES, TOSYLATED IN THE CARBOHYDRATE MOIETY, WITH LITHIUM TRIETHYLBOROHYDRIDE

The reaction of lithium triethylborohydride with the 2',3'-di-O-p-tolylsulphonyl derivatives of 9-β-D-ribofuranosyladenine, 9-β-D-arabinofuranosyladenine, 9-β-D-xylofuranosyladenine and 9-β-D-lyxofuranosyladenine was studied.The reaction of 2',3'-di-O-p-tolylsulphonyladenosine with LiEt3BH gave 9-(3-deoxy-β-D-threo-pentofuranosyl)adenine.This rearrangement reaction was used for the synthesis of 9-(3,5-dideoxy-β-D-threo-pentofuranosyl)adenine in one step from 2',3',5'-tri-O-p-tolylsulphonyladenosine in 58percent yield.The p-tolylsulphonyl group in the 2'-"up" configuration of unprotected adenine nucleosides was preferentially attacked by LiEt3BH giving S-O-bond scission.This was shown by the formation of 9-(3-deoxy-β-D-threo-pentofuranosyl)adenine from 2',3'-di-O-p-tolylsulphonyl-9-β-D-arabinofuranosyladenine and by the formation of 9-β-D-lyxofuranosyladenine from 2'-O-p-tolylsulphonyl-9-β-D-lyxofuranosyladenine with LiEt3BH. 9-β-D-Lyxofuranosyladenine was synthesized from 3',5'-di-O-benzoyl-9-β-D-xylofuranosyladenosine in 88percent yield using a triflate displacement reaction.